2,433

Cudjoe Key, FL Homes

Section Image
    • 21541 Asturias Rd, Summerland Key, FL 33042
      21541 Asturias Rd, Summerland Key, FL 33042
      21541 Asturias Rd, Summerland Key, FL 33042
      /16

      Est $914,745 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft

      21541 Asturias Rd, Summerland Key, FL 33042

      21541 Asturias Rd, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
    /24

    $606,995

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

    Motivated seller! Possible Seller Financing. Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both

    Sarah Dolson Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
    • 21056 3rd Ave, Summerland Key, FL 33042
      21056 3rd Ave, Summerland Key, FL 33042
      /2

      Est $1,207,766 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,726 Sq Ft

      21056 3rd Ave, Summerland Key, FL 33042

      21056 3rd Ave, Summerland Key, FL 33042
  • 246 Colson Dr, Summerland Key, FL 33042
    246 Colson Dr, Summerland Key, FL 33042
    246 Colson Dr, Summerland Key, FL 33042
    /66

    $998,000

    • 3 Beds
    • 2 Baths
    • 1,541 Sq Ft

    246 Colson Dr, Summerland Key, FL 33042

    SPECTACULAR OCEANVIEWS!!! Just a few houses in from the Wide Open Ocean & Bay- CBS House 3 Bed/2 Bath - 80 ft. Concrete Dock on a Deep - Water -Wide - Canal. Beautifully Landscaped Yard. This home features - Cathedral Ceilings, Custom Cabinets & Island. Great Layout, & Impeccable Craftmanship on the Front Door & Tile through out. Plenty of Room for a Pool, RV, & All your toys. Quiet

    Tracey Petrusha Venture Realty Group

    246 Colson Dr, Summerland Key, FL 33042
    • 113 Galleon Ln, Summerland Key, FL 33042
      113 Galleon Ln, Summerland Key, FL 33042
      /2

      Est $1,284,176 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,042 Sq Ft

      113 Galleon Ln, Summerland Key, FL 33042

      113 Galleon Ln, Summerland Key, FL 33042
  • 37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
    37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
    /2

    $450,000

    • 2 Beds
    • 2 Baths
    • 980 Sq Ft

    37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

    This sale is for three 5000 square foot lots. Two are undeveloped (bilders points TBD) One lot has an abandoned house so it is ROGO exempt.

    Joseph Ordini Keller Williams Key West Compass Realty

    37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
    • 172 Galleon Ln, Summerland Key, FL 33042
      172 Galleon Ln, Summerland Key, FL 33042
      172 Galleon Ln, Summerland Key, FL 33042
      /32

      Est $864,919 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,232 Sq Ft

      172 Galleon Ln, Summerland Key, FL 33042

      172 Galleon Ln, Summerland Key, FL 33042
  • 248 Yardarm Rd, Cudjoe Key, FL 33042
    248 Yardarm Rd, Cudjoe Key, FL 33042
    /2

    $450,000

    • Land

    248 Yardarm Rd, Cudjoe Key, FL 33042

    The sale is for lots 35,36, & 37. Lot 37 has a house that is rogo exempt. Sewer is being connected and the lots will be cleared and cleaned. The two other lots have a total of 1 to 2 transferable points attached(to be determined)

    Joseph Ordini Keller Williams Key West Compass Realty

    248 Yardarm Rd, Cudjoe Key, FL 33042
    • 21012 6th Ave, Summerland Key, FL 33042
      21012 6th Ave, Summerland Key, FL 33042
      21012 6th Ave, Summerland Key, FL 33042
      /33

      Est $1,116,662 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,372 Sq Ft

      21012 6th Ave, Summerland Key, FL 33042

      21012 6th Ave, Summerland Key, FL 33042
  • 21161 Old State Road 4a, Summerland Key, FL 33042
    21161 Old State Road 4a, Summerland Key, FL 33042
    /2

    $719,000

    • 2 Beds
    • 2 Baths
    • 855 Sq Ft

    21161 Old State Road 4a, Summerland Key, FL 33042

    PRIME OPPORTUNITY IN CUDJOE KEY! Elevated home boasts 2 spacious bedrooms and 2 recently renovated baths.

    Bascom Grooms Bascom Grooms Real Estate (KW)

    21161 Old State Road 4a, Summerland Key, FL 33042
    • 20880 6th Ave W, Summerland Key, FL 33042
      20880 6th Ave W, Summerland Key, FL 33042
      20880 6th Ave W, Summerland Key, FL 33042
      /42

      Est $1,623,545 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,761 Sq Ft

      20880 6th Ave W, Summerland Key, FL 33042

      20880 6th Ave W, Summerland Key, FL 33042
  • 23066 Tarpon Ln, Summerland Key, FL 33042
    23066 Tarpon Ln, Summerland Key, FL 33042
    23066 Tarpon Ln, Summerland Key, FL 33042
    /36

    $2,400,000 New Construction

    • 4 Beds
    • 4 Baths
    • 1,938 Sq Ft

    23066 Tarpon Ln, Summerland Key, FL 33042

    ''BRAND NEW' CBS Construction ready for occupancy!!! Amazing New Oceanside Home with 4 Bedrooms, 3.5 Baths, in Beautiful Cudjoe Ocean Shores, (Custom Built by Dream Builders of the Florida Keys). This home offers Open Water Views, Instant Deep Draft Boating for Big Boat Action, Protected Concrete step-down Dock, Open Floor plan, Dining Area, two Master Suites, High Ceilings, Chefs Kitchen with

    Greg MacLaren Internet Realty of the Florida Keys

    23066 Tarpon Ln, Summerland Key, FL 33042
    • 429 Sawyer Dr, Summerland Key, FL 33042
      429 Sawyer Dr, Summerland Key, FL 33042
      /2

      Est $2,290,107 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,999 Sq Ft

      429 Sawyer Dr, Summerland Key, FL 33042

      429 Sawyer Dr, Summerland Key, FL 33042
  • 220 E Caribbean Dr, Summerland Key, FL 33042
    220 E Caribbean Dr, Summerland Key, FL 33042
    220 E Caribbean Dr, Summerland Key, FL 33042
    /107

    $5,992,000 New Construction

    • 5 Beds
    • 7 Baths
    • 4,981 Sq Ft

    220 E Caribbean Dr, Summerland Key, FL 33042

    Experience unparalleled luxury in this Brand New 2025 Custom Built Smart Home. 6,128 SQ FT concrete-constructed oceanfront home, situated in prestigious Summerland Key. With 90 feet of ocean frontage and breathtaking southwest views of the Atlantic Ocean, this home is the ultimate retreat for those seeking elegance, comfort, and adventure.The third floor is the heart of this home, featuring an

    Stacy Shahan Island Real Estate Company Florida Keys

    220 E Caribbean Dr, Summerland Key, FL 33042
    • 22808 Privateer Dr, Summerland Key, FL 33042
      22808 Privateer Dr, Summerland Key, FL 33042
      /2

      Est $944,744 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,454 Sq Ft

      22808 Privateer Dr, Summerland Key, FL 33042

      22808 Privateer Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    /29

    $415,000 Pending

    • Land

    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

    Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Buildable RV Lot. Nestled in a serene, well-maintained community, this RV lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a 35' concrete seawall, dock posts, swim ladder, full hookups including water, sewer, and 30, 50 and 110 amp electric service. Enjoy the convenience of a

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    • 22964 Anne Bonny Ln, Summerland Key, FL 33042
      22964 Anne Bonny Ln, Summerland Key, FL 33042
      22964 Anne Bonny Ln, Summerland Key, FL 33042
      /29

      Est $755,739 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft

      22964 Anne Bonny Ln, Summerland Key, FL 33042

      22964 Anne Bonny Ln, Summerland Key, FL 33042
  • 366 Sawyer Dr, Summerland Key, FL 33042
    366 Sawyer Dr, Summerland Key, FL 33042
    366 Sawyer Dr, Summerland Key, FL 33042
    /41

    $1,200,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,390 Sq Ft

    366 Sawyer Dr, Summerland Key, FL 33042

    Welcome to your own tropical paradise! This stunning oceanside retreat offers everything you need for the ultimate waterfront lifestyle. With an 80-ft concrete dock, you'll have plenty of space for your boat, making it easy to set off on incredible fishing adventures--just minutes to the open ocean via direct canal or the serene backcountry waters.This inviting 3-bedroom, 2-bathroom home is

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    366 Sawyer Dr, Summerland Key, FL 33042
    • 22928 Drake Ln, Summerland Key, FL 33042
      22928 Drake Ln, Summerland Key, FL 33042
      /2

      Est $1,754,776 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,128 Sq Ft

      22928 Drake Ln, Summerland Key, FL 33042

      22928 Drake Ln, Summerland Key, FL 33042
  • 531 Seminole Dr, Summerland Key, FL 33042
    531 Seminole Dr, Summerland Key, FL 33042
    531 Seminole Dr, Summerland Key, FL 33042
    /62

    $2,999,999 Under Contract

    • 4 Beds
    • 3 Baths
    • 2,604 Sq Ft

    531 Seminole Dr, Summerland Key, FL 33042

    Welcome to this stunning CBS (Concrete Block Stucco) Home located in the desirable Cudjoe Gardens neighborhood on Cudjoe Key. This charming 4-bedroom, 3-bathroom residence offers 255 feet of seawall, perfect for boating enthusiasts with ample dock space and 2 boat lifts. As you approach this meticulously landscaped property, on a lot & half, you'll be greeted by the serene ambiance of the

    Beata Sharpe COLDWELL BANKER VANGUARD REALTY

    531 Seminole Dr, Summerland Key, FL 33042
    • 20761 2nd Ave W, Summerland Key, FL 33042
      20761 2nd Ave W, Summerland Key, FL 33042
      20761 2nd Ave W, Summerland Key, FL 33042
      /44

      Est $1,565,180 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,777 Sq Ft

      20761 2nd Ave W, Summerland Key, FL 33042

      20761 2nd Ave W, Summerland Key, FL 33042
  • 531 Seminole Dr, Summerland Key, FL 33042
    531 Seminole Dr, Summerland Key, FL 33042
    531 Seminole Dr, Summerland Key, FL 33042
    /68

    $2,999,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 2,604 Sq Ft

    531 Seminole Dr, Summerland Key, FL 33042

    Welcome to this stunning CBS (Concrete Block Stucco) Home located in the desirable Cudjoe Gardens neighborhood on Cudjoe Key. This charming 4-bedroom, 3-bathroom residence offers 255 feet of seawall, perfect for boating enthusiasts with ample dock space and 2 boat lifts.As you approach this meticulously landscaped property, on a lot & half, you'll be greeted by the serene ambiance of the tropical

    Karen Haack Coldwell Banker Schmitt RE Co. Lower Keys Office

    531 Seminole Dr, Summerland Key, FL 33042
    • 23032 Snapper Ln, Summerland Key, FL 33042
      23032 Snapper Ln, Summerland Key, FL 33042
      23032 Snapper Ln, Summerland Key, FL 33042
      /25

      Est $1,177,599 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      23032 Snapper Ln, Summerland Key, FL 33042

      23032 Snapper Ln, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042
    /46

    $589,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 754 Sq Ft

    701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042

    This super cute, meticulous maintained property is all you need to start living and enjoying paradise in the Florida Keys. It comes completely furnished with coastal charm and includes 2 bedrooms and 2 baths, a stunning kitchen and dining room and views out to the patio overlooking the canal. The patio is perfect for those beautiful evenings outside for entertaining, grilling, or sipping adult

    Jan Fritz Coldwell Banker Schmitt RE Co. Lower Keys Office

    701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042
    • 1273 Rogers Ln, Summerland Key, FL 33042
      1273 Rogers Ln, Summerland Key, FL 33042
      1273 Rogers Ln, Summerland Key, FL 33042
      /49

      Est $4,319,554 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 1,280 Sq Ft

      1273 Rogers Ln, Summerland Key, FL 33042

      1273 Rogers Ln, Summerland Key, FL 33042
  • 22971 Hawkins Ln, Summerland Key, FL 33042
    22971 Hawkins Ln, Summerland Key, FL 33042
    22971 Hawkins Ln, Summerland Key, FL 33042
    /38

    $949,900 Under Contract

    • 3 Beds
    • 3 Baths
    • 1,142 Sq Ft

    22971 Hawkins Ln, Summerland Key, FL 33042

    Don't miss this immaculate home at 22971 Hawkins Ln Cudjoe Key. This completely furnished 3 bedroom 3 bath home is in impeccable condition with recent upgrades to include all new kitchen and appliances, new baths, impact windows, AC, metal roof and paint. The third bedroom could be utilized as an office, gym, yoga or media room. The home also has a walk around deck with a covered screened porch.

    Greg MacLaren Internet Realty of the Florida Keys

    22971 Hawkins Ln, Summerland Key, FL 33042
    • 22944 Lookdown Ln, Summerland Key, FL 33042
      22944 Lookdown Ln, Summerland Key, FL 33042
      /2

      Est $1,944,260 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,224 Sq Ft

      22944 Lookdown Ln, Summerland Key, FL 33042

      22944 Lookdown Ln, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
    /59

    $949,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

    This home is BIG BOAT friendly and ready for you to move in. Turn key, fully furnished home located in the gated community of Venture Out on Cudjoe Key at Mile Marker 23. 2 Bedrooms and 2 Baths mid-rise sits on open water with an oversized massive 60' of concrete seawall. When you walk inside, you will feel like you are floating on the ocean with the large windows and picturesque ocean views. The

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
    • 22856 Cudjoe Dr, Summerland Key, FL 33042
      22856 Cudjoe Dr, Summerland Key, FL 33042
      22856 Cudjoe Dr, Summerland Key, FL 33042
      /43

      Est $833,699 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,350 Sq Ft

      22856 Cudjoe Dr, Summerland Key, FL 33042

      22856 Cudjoe Dr, Summerland Key, FL 33042
    • VACANT LAND LOT 16 Avon Ave, Other Fl Key, FL 33042
      VACANT LAND LOT 16 Avon Ave, Other Fl Key, FL 33042
      VACANT LAND LOT 16 Avon Ave, Other Fl Key, FL 33042
      /4

      Not Listed For Sale

      VACANT LAND LOT 16 Avon Ave, Other Fl Key, FL 33042

      VACANT LAND LOT 16 Avon Ave, Other Fl Key, FL 33042
    • Vacant land lot 15 Avon Ave, Other Fl Key, FL 33042
      Vacant land lot 15 Avon Ave, Other Fl Key, FL 33042
      Vacant land lot 15 Avon Ave, Other Fl Key, FL 33042
      /4

      Not Listed For Sale

      Vacant land lot 15 Avon Ave, Other Fl Key, FL 33042

      Vacant land lot 15 Avon Ave, Other Fl Key, FL 33042
    • 701 Spanish Main Dr Unit 456, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 456, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 456, Cudjoe Key, FL 33042
      /47

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 498 Sq Ft

      701 Spanish Main Dr Unit 456, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 456, Cudjoe Key, FL 33042
    • 22980 Gasparilla Ln, Cudjoe Key, FL 33042
      22980 Gasparilla Ln, Cudjoe Key, FL 33042
      22980 Gasparilla Ln, Cudjoe Key, FL 33042
      /13

      Not Listed For Sale

      22980 Gasparilla Ln, Cudjoe Key, FL 33042

      22980 Gasparilla Ln, Cudjoe Key, FL 33042
    • 510 Seminole Dr, Summerland Key, FL 33042
      510 Seminole Dr, Summerland Key, FL 33042
      510 Seminole Dr, Summerland Key, FL 33042
      /41

      Est $3,547,970 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,907 Sq Ft

      510 Seminole Dr, Summerland Key, FL 33042

      510 Seminole Dr, Summerland Key, FL 33042
    • 701 Spanish Main Dr Unit 379, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 379, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 379, Cudjoe Key, FL 33042
      /42

      Est $556,653 Not Listed For Sale

      • 1 Bed

      701 Spanish Main Dr Unit 379, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 379, Cudjoe Key, FL 33042
    • 0 Sawyer Dr, Cudjoe Key, FL 33042
      0 Sawyer Dr, Cudjoe Key, FL 33042
      0 Sawyer Dr, Cudjoe Key, FL 33042
      /12

      Not Listed For Sale

      0 Sawyer Dr, Cudjoe Key, FL 33042

      0 Sawyer Dr, Cudjoe Key, FL 33042
    • 701 Spanish Main Dr Unit LOT 608, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit LOT 608, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit LOT 608, Cudjoe Key, FL 33042
      /37

      Not Listed For Sale

      • 1 Bed
      • 1.5 Baths
      • 552 Sq Ft

      701 Spanish Main Dr Unit LOT 608, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit LOT 608, Cudjoe Key, FL 33042
    • 1078 Picard Ln, Cudjoe Key, FL 33042
      1078 Picard Ln, Cudjoe Key, FL 33042
      /2

      Est $1,181,525 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,488 Sq Ft

      1078 Picard Ln, Cudjoe Key, FL 33042

      1078 Picard Ln, Cudjoe Key, FL 33042
    • 701 Spanish Main Dr Unit 106, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 106, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 106, Cudjoe Key, FL 33042
      /45

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 816 Sq Ft

      701 Spanish Main Dr Unit 106, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 106, Cudjoe Key, FL 33042
    • 0 Overseas Hwy, Cudjoe Key, FL 33042
      0 Overseas Hwy, Cudjoe Key, FL 33042
      0 Overseas Hwy, Cudjoe Key, FL 33042
      /4

      Not Listed For Sale

      0 Overseas Hwy, Cudjoe Key, FL 33042

      0 Overseas Hwy, Cudjoe Key, FL 33042

Showing Results 281 - 320, Page 8 of 18

Florida Cudjoe Key

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group